Methanol → 5-Bromo-2-hydroxy-3-methylbenzoic acid

HRID 391443

Reaction equation

HRID 391443 reaction equation
[OH:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:12]Br.O.CO>C(O)(=O)C>[Br:12][C:8]1[CH:9]=[C:10]([CH3:11])[C:2]([OH:1])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 887Methanol2×HCID 962WaterHCID 67383-Methylsalicylic AcidHCID 24408Bromine

Product 1

HCID 27643455-Bromo-2-hydroxy-3-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 2-hydroxy-3-methylbenzoic acid (2.1 g, 13.5 mmol) in acetic acid (30 mL) was added bromine (0.7 mL, 13.7 mmol) slowly over 5 minutes. After 24 h, water was added slowly to the reaction mixture and the reaction stirred for 30 min. The resulting precipitate was collected by filtration and washed several times with water. The product was dried overnight under high vacuum to afford 2.8 g (90%). LC/MS: tR=2.86 min, 229.14 (MH)+. (Phenomenex C18 4.6×50 mm, 10% MeOH/90% H2O/0.1% TFA→90% MeOH/10% H2O/0.1% TFA, Gradient time=4 min., Flow rate=4 mL/min.).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed several times with water
  3. customThe product was dried overnight under high vacuum
  4. customto afford 2.8 g (90%)

Sources & evidence

ORD record
ord-c43b7d30147e43818ccab92c88f481e1
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Linked notes

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